Picolo recommends · Hotel in Key West, Florida
Winslow's Bungalows
Restored clapboard houses in Old Town, gathered around three pools and a garden, five minutes from Duval Street.
Winslow's Bungalows is a group of old wooden houses in Old Town, restored and set around a garden with three pools and a bar by the water. It belongs to Key West Historic Inns, which runs several small hotels in historic buildings.
Rooms and suites are spread across the houses, so you get space and quiet while Duval Street stays a short walk away.
Picolo’s verdict
Why we chose Winslow's Bungalows
Winslow's gives you the old town feeling at a more relaxed level than The Marquesa, with more pools and room to spread out with friends.
Rooms differ from house to house, and there is no beach. Check the room type carefully before you book.
What you get
- Three outdoor pools
- Bar by the pool
- Restored wooden houses
- Garden
- Five minutes from Duval on foot
A day at Winslow's Bungalows
- Morning
- Coffee on the porch of your bungalow.
- Midday
- A swim in one of the three pools.
- Afternoon
- A walk through the quiet lanes of Old Town.
- Evening
- A drink at the pool bar before heading to Duval.
Location
Key West, Florida, USA
Open in MapsQuestions about Winslow's Bungalows
How many pools does Winslow's Bungalows have?
There are three outdoor pools, as well as a bar by the pool.
Is Winslow's Bungalows in Old Town?
Yes, it is in Old Town, about five minutes on foot from Duval Street.
Does Winslow's Bungalows have a beach?
No. The nearest beaches are a short bike ride away.
Would you rather stay somewhere else?
Three other Key West hotels, each picked for a different reason.
Updated 5 Nov 2026All articles
How Picolo chooses
Our editors pick every hotel themselves, and most of them we have stayed at. No hotel can pay to be included or ranked higher. When you book through our links, Hotels.com pays Picolo a small commission. It never changes the price you pay, and it never decides what we write.
